Epicriptine

Epicriptine
Clinical data
Synonyms	beta-Dihydroergocryptine
Pregnancy; category	Contraindicated;
Routes of; administration	Oral
ATC code	N04BC03 (WHO) (alpha/beta);
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (2R,4R,7R)-N- [(1S,2S,4R,7S)- 2-hydroxy- 7-(S)-(1-methylpropyl)- 5,8-dioxo- 4-(propan-2-yl)- 3-oxa- 6,9-diazatricyclo [7.3.0.02,6]dodecan-4-yl]- 6-methyl- 6,11-diazatetracyclo [7.6.1.02,7.012,16] hexadeca- 1(16),9,12,14-tetraene- 4-carboxamide;
CAS Number	19467-62-0;
PubChem CID	3084313;
ChemSpider	2341400;
UNII	5M64643B5U;
ChEBI	CHEBI:59925;
ChEMBL	CHEMBL1378681;
ECHA InfoCard	100.039.157
Chemical and physical data
Formula	C32H43N5O5
Molar mass	577.715 g/mol
3D model (JSmol)	Interactive image;
	SMILES CCC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4C[C@H]5[C@@H](CC6=CNC7=CC=CC5=C67)N(C4)C)O;
	InChI InChI=1S/C32H43N5O5/c1-6-18(4)27-29(39)36-12-8-11-25(36)32(41)37(27)30(40)31(42-32,17(2)3)34-28(38)20-13-22-21-9-7-10-23-26(21)19(15-33-23)14-24(22)35(5)16-20/h7,9-10,15,17-18,20,22,24-25,27,33,41H,6,8,11-14,16H2,1-5H3,(H,34,38)/t18?,20-,22-,24-,25+,27+,31-,32+/m1/s1; Key:SBFXHXZNBNFPHV-CROXOCCCSA-N;

Epicriptine or beta-dihydroergocryptine is a dopamine agonist of the ergoline class. It constitutes one third of the mixture known as dihydroergocryptine, the other two thirds consisting of alpha-dihydroergocryptine. The alpha differs from the beta form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid isoleucine is replaced by leucine.^[1]

References

↑ Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 142. ISBN 3-7692-3483-9.

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[1] Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005). Medizinische Chemie (in German). Stuttgart: Deutscher Apotheker Verlag. p. 142. ISBN 3-7692-3483-9.

Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergotamine Ergotoxine Ergovaline Lisuride LSD LSH Lysergic Acid Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Pergolide Syntometrine
Psychedelic lysergamides	1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 Ergonovine ETH-LAD IP-LAD LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergonovine Methylisopropyllysergamide MLD-41 PARGY-LAD PRO-LAD
clavines	agroclavine elymoclavine lysergol festuclavine fumigaclavine A fumigaclavine B fumigaclavine C
Other ergolines	Ergoline
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

Clinical data

Synonyms	beta-Dihydroergocryptine
Pregnancy category	Contraindicated
Routes of administration	Oral
ATC code	N04BC03 (WHO) (alpha/beta)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (2R,4R,7R)-N- [(1S,2S,4R,7S)- 2-hydroxy- 7-(S)-(1-methylpropyl)- 5,8-dioxo- 4-(propan-2-yl)- 3-oxa- 6,9-diazatricyclo [7.3.0.0^2,6]dodecan-4-yl]- 6-methyl- 6,11-diazatetracyclo [7.6.1.0^2,7.0^12,16] hexadeca- 1(16),9,12,14-tetraene- 4-carboxamide
CAS Number	19467-62-0
PubChem CID	3084313
ChemSpider	2341400
UNII	5M64643B5U
ChEBI	CHEBI:59925
ChEMBL	CHEMBL1378681
ECHA InfoCard	100.039.157
Chemical and physical data
Formula	C₃₂H₄₃N₅O₅
Molar mass	577.715 g/mol
3D model (JSmol)	Interactive image
SMILES CCC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4C[C@H]5[C@@H](CC6=CNC7=CC=CC5=C67)N(C4)C)O
InChI InChI=1S/C32H43N5O5/c1-6-18(4)27-29(39)36-12-8-11-25(36)32(41)37(27)30(40)31(42-32,17(2)3)34-28(38)20-13-22-21-9-7-10-23-26(21)19(15-33-23)14-24(22)35(5)16-20/h7,9-10,15,17-18,20,22,24-25,27,33,41H,6,8,11-14,16H2,1-5H3,(H,34,38)/t18?,20-,22-,24-,25+,27+,31-,32+/m1/s1 Key:SBFXHXZNBNFPHV-CROXOCCCSA-N